Hey @zach3 this seems quite baffling and it got my interest, as I will be working soon with booking situations.
Is there any chance I can have access to your editor to take a peek and add a new set of eyes?
Also, when you tried changing your timezone and could replicate the error, did you look into the debugger to what was being displayed on the repeating group? This kind of has the looks of Privacy Rules (although it doesn’t seem to make sense).